Stereoselective synthesis of electrophilic spirocyclopropanes in ionic liquids

被引:38
作者
Calò, V [1 ]
Nacci, A [1 ]
Lopez, L [1 ]
Lerario, VL [1 ]
机构
[1] Univ Bari, Dipartmento Chim, Ctr CNR MISO, I-70126 Bari, Italy
关键词
cyclopropanation; stereocontrol; ionic liquids; benzothiazole; sulfides;
D O I
10.1016/S0040-4039(00)01593-8
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The reaction of beta -oxosulfides of benzothiazole with Michael accepters, in liquid tetrabutylammonium bromide and sodium bicarbonate as base, allows a stereoselective synthesis of spirocyclopropanes. (C) 2000 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:8977 / 8980
页数:4
相关论文
共 14 条
[1]  
AHLBRECHT H, 1988, SYNTHESIS-STUTTGART, P210
[2]   Asymmetric cyclopropanation reaction under phase-transfer catalyzed conditions [J].
Arai, S ;
Nakayama, K ;
Ishida, T ;
Shioiri, T .
TETRAHEDRON LETTERS, 1999, 40 (22) :4215-4218
[3]   FORMATION OF CYCLOPROPANES IN GAMMA-ELIMINATION REACTIONS OF SULPHOXIDES [J].
BAKER, R ;
SPILLETT, MJ .
CHEMICAL COMMUNICATIONS, 1966, (20) :757-&
[4]   Allylated ketosulphides of benzothiazole as intermediates for stereoselective synthesis of allyl ketones, allyl thiiranes and dienes [J].
Calo, V ;
Fiandanese, V ;
Nacci, A ;
Volpe, A .
TETRAHEDRON, 1996, 52 (06) :2155-2166
[5]   ELECTROPHILIC CYCLOPROPANES IN ORGANIC-SYNTHESIS [J].
DANISHEFSKY, S .
ACCOUNTS OF CHEMICAL RESEARCH, 1979, 12 (02) :66-72
[6]  
DEMEIJER A, 1997, HOUBEN WEYL METHOD E, V17
[7]   SOLVENT EFFECT IN A PARTIAL ASYMMETRIC SYNTHESIS .I. [J].
INOUYE, Y ;
INAMASU, S ;
HORIIKE, M ;
OHNO, M .
TETRAHEDRON, 1968, 24 (07) :2907-&
[8]  
JONCZYK A, 1976, SYNTHESIS-STUTTGART, P387
[9]   NOVEL SYNTHESIS OF METHYL CARONATE [J].
KRIEF, A ;
DEVOS, MJ ;
SEVRIN, M .
TETRAHEDRON LETTERS, 1986, 27 (20) :2283-2286
[10]   2-LITHIO-2-PHENYLSULFONYL PROPANE AS EFFICIENT PRECURSOR OF GEM-DIMETHYL CYCLOPROPANE CARBOXYLIC-ACIDS [J].
KRIEF, A ;
DEVOS, MJ .
TETRAHEDRON LETTERS, 1985, 26 (49) :6115-6116